
Vacation rentals in Hillsborough
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Top-rated vacation rentals in Hillsborough
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Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Peaceful Mill with Waterfall - Home Away From Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Newer Home on quiet 200 acre lake - sleeps 6
Less than an hour from Manchester, Concord & Keene, this new home offers relaxation & year-round adventure. This lakefront property has a dock, with kayaks & paddleboards. You could also walk down the paved road to the neighborhood beach & swim platform. About 30 minutes to Pats Peak, Sunapee, or Crotched Mtn ski resorts. Beds for 6, 2 full baths, W/D, fully equipped kitchen, open living space, gas fireplace, water views, gas grill, parking, firepit, internet. We do not allow pets or smoking.

The SugarShack at Sweetwater
Welcome to our off-the-grid cabin, sleeping 2-4 people with an upstairs loft & downstairs custom Murphy bed. It's equipped with lights, mini-fridge, Bluetooth speakers & an indoor/outdoor bar. Outside you'll find a private fire pit & charcoal grill, a shared outdoor kitchen pavilion w/ gas grill (stocked with cooking supplies) & the outdoor bathroom w/ a real flushing toilet, sink and outdoor shower. Access the Tooky River just steps away and enjoy plenty of space, privacy & beautiful scenery!

Deer Valley Retreat, Lovely Log Cabin
This Lake Sunapee Region cabin retreat is perfect for romantics, artists, writers, outdoor enthusiasts, gardeners, friends, & family. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities. Still, the cabin feels like a destination in itself, where you can relax, recharge, and reconnect. Cozy up by the stone fireplace, relax on the porch, see nature, read, listen, play, cook, stargaze, and enjoy just being! M&R license #: 063685

Private Dublin apartment nestled in the woods
Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

Large Private Lake House
Spacious lake house with a private beach, directly on Lake Todd in Newbury, NH, located within the Lake Sunapee Region. Fish for bass, pickerel or swim/boat to one of the lake's three islands. Relax on the water or on one of the large decks overlooking the lake. Enjoy local outdoor activities such as hiking, biking, golfing, fishing & kayaking. Mt Sunapee ski area is only 10 minutes down the road. Enjoy ice skating and cross country skiing right out your door in the winter or cozy by the fire.

Elegant Lodging in the Woods ~Privacy & Comfort!
Looking for a relaxing escape? As Superhosts with 6 years of 5-star reviews, we warmly welcome you to our private, smoke free guest suite. Perfect for couples or solo travelers seeking comfort & tranquility. Tucked away in the peaceful countryside near Pat's Peak & Crotched Mountain, our location offers convenient access to scenic lakes, golfing, hiking, skiing and the charm of rural New England. Enjoy the comfort of serene surroundings & experience genuine hospitality. 75 minutes from Boston.

Direct Waterfront A-Frame, Close to 3 Ski Areas!
My direct waterfront, year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s located on a small 32-acre pond near Franklin Pierce Lake with over 100 feet of waterfront. There is a 6 foot main dock to load kayaks, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! The property sits on 1/3 of an acre, on a sloped hill. It's located between Keene and Concord, and nearby many great hiking and snowmobile trails

Tranquil Getaway-Dartmouth Lake Sunapee Region
Welcome to your picturesque, peaceful getaway! Nestled along a historic country road, this charming, rustic cottage style home is just minutes from skiing at Mount Sunapee (6 mi), Pats Peak (12 mi), and many other nearby ski areas. Easy access to a network of scenic trails for hiking, snow shoeing, and snowmobiling to explore. Enjoy nearby pristine lakes like beautiful Lake Sunapee, or just relax and soak in the beautiful views — a perfect destination to make memories in any season!

Bog Mt Retreat Upstairs Suite
A unique crafty cozy 1 bedroom/1 bathroom UPSTAIRS suite with most of the comforts of home except a oven. Woodland trails on the property, moderate hikes nearby or bring your kayaks and explore the many ponds and lakes in the area. Ragged Mt and Mt Sunapee Ski Resorts are both under 30 minutes away. This uniquely designed suite is perfect for an individual or couple wanting to escape into the country but still be within an easy driving distance to local sites.

Highland Haus | Cozy 70s Aframe | Lake Access
Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!
Popular amenities for Hillsborough vacation rentals
Other great vacation rentals in Hillsborough

Hidden Gem: Amazing lake house + all the amenities

The Cozy Place

Charming Woodland Hideaway

Breezy Hill

A Lovely In-Law Apt Near Pat’s Peak and NEC!

Lake house getaway

Modern Chalet with Lake Access, Kayaking

Mtn Mtn Cabin. Log home with forever views.
Destinations to explore
- Plainview Vacation rentals
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- East River Vacation rentals
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- Okemo Mountain Resort
- Squam Lake
- Weirs Beach
- Pats Peak Ski Area
- Monadnock State Park
- Canobie Lake Park
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Gunstock Mountain Resort
- Snhu Arena
- Ragged Mountain Resort
- Bear Brook State Park
- Fox Run Golf Club
- Dartmouth College
- Squam Lakes Natural Science Center
- Montshire Museum of Science
- Mount Sunapee Resort
- Ellacoya State Park
- Mount Monadnock
- Plymouth State University
- Camp Plymouth State Park
- Dunn State Park
- Tsongas Center
- Quechee Gorge





